Crystal structure determination and Hirshfeld surface analysis of N-acetyl-N-3-meth­oxy­phenyl and N-(2,5-di­meth­oxy­phen­yl)-N-phenyl­sulfonyl derivatives of N-[1-(phenyl­sulfon­yl)-1H-indol-2-yl]methanamine

Madhan, S.; NizamMohideen, M.; Pavunkumar, V.; MohanaKrishnan, A.K.

doi:10.1107/S2056989024006649

research communications

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ISSN: 2056-9890

Volume 80| Part 8| August 2024| Pages 845-851

https://doi.org/10.1107/S2056989024006649

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Crystal structure determination and Hirshfeld surface analysis of N-acetyl-N-3-methoxyphenyl and N-(2,5-dimethoxyphenyl)-N-phenylsulfonyl derivatives of N-[1-(phenylsulfonyl)-1H-indol-2-yl]methanamine

S. Madhan,^a M. NizamMohideen,^a ^* Vinayagam Pavunkumar ^b and Arasambattu K. MohanaKrishnan ^b

^aDepartment of Physics, The New College, Chennai 600 014, University of Madras, Tamil Nadu, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-600 025, Tamilnadu, India
^*Correspondence e-mail: mnizam.new@gmail.com

Edited by K. V. Domasevitch, National Taras Shevchenko University of Kyiv, Ukraine (Received 14 June 2024; accepted 5 July 2024; online 9 July 2024)

Two new [1-(phenylsulfonyl)-1H-indol-2-yl]methanamine derivatives, namely, N-(3-methoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}acetamide, C₂₄H₂₂N₂O₄S, (I), and N-(2,5-dimethoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide, C₂₉H₂₆N₂O₆S₂, (II), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C—H⋯O bonding [C⋯O = 3.312 (4)–3.788 (8) Å], with the structure of II exhibiting a larger number, but weaker bonds of this type. Slipped π–π interactions of antiparallel indole systems are specific for I, whereas the structure of II delivers two kinds of C—H⋯π interactions at both axial sides of the indole moiety. These findings agree with the results of Hirshfeld surface analysis. The primary contributions to the surface areas are associated with the contacts involving H atoms. Although II manifests a larger fraction of the O⋯H/H⋯O contacts (25.8 versus 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations.

Keywords: crystal structure; 1H-indole; acetamide; phenylsulfonamide; hydrogen bonding; Hirshfeld surface analysis.

CCDC references: 2368308; 2368307

1. Chemical context

Derivatives of indole exhibit antibacterial (Okabe & Adachi, 1998 ) and antitumour (Schollmeyer et al., 1995 ) activities. In particular, 1-(phenylsulfonyl)indoles are applicable to the synthesis of biologically active alkaloids, such as the anticancer alkaloid ellipticine, carbazoles, furoindoles, pyrroloindoles, indolocarbazoles and their analogues, including pyridocarbazoles. Some of the phenylsulfonyl indole compounds have been shown to inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993 ). In such systems, the phenylsulfonyl moiety can act either as a protecting or an activating group (Jasinski et al., 2010 ). Ring-substituted acetanilides are valuable synthetic intermediates (Gowda et al., 2007 ) that are used as precursors for the preparation of many heterocyclic compounds (Wen et al., 2006 ). The amide linkage [–NHC(O)–] is known for its importance in maintaining protein architectures and it has been utilized in the development of molecular devices for a spectrum of purposes in organic chemistry (NizamMohideen, SubbiahPandi et al., 2009 ; NizamMohideen et al., 2009a ,b ). Benzenesulfonamide derivatives exhibit antitumor (Yang et al., 2002 ), anti-bacterial (Badr, 2008 ) and anti-fungal (Hanafy et al., 2007 ) activities. Recognizing the importance of such compounds for biochemical applications and drug discovery and our ongoing research into the construction of indole derivatives have prompted us to investigate a series of corresponding methoxyphenyl-substituted species. We report herein the crystal structure determination and Hirshfeld surface analysis of two new (1-(phenylsulfonyl)-1H-indol-2-yl)methanamine derivatives: N-(3-methoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}acetamide (I) and N-(2,5-dimethoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide (II).

2. Structural commentary

The molecular structures of the title compounds, which differ in the substituents at the exocyclic nitrogen atoms N2 [N-acetyl-N-3-methoxyphenyl (I) and N-phenylsulfonyl-N-(2,5-dimethoxyphenyl) (II)], are illustrated in Figs. 1 and 2, respectively. In both compounds, the indole ring system (N1/C1–C8) is essentially planar, with maximum deviations from the corresponding mean planes of 0.027 (3) and 0.017 (5) Å observed for atoms C8 in I and C1 in II. The sulfonyl-bound phenyl rings (C9–C14) are almost orthogonal to the carrier indole ring systems (N1/C1–C8), with respective interplanar angles of 83.9 (2)° for I and 83.5 (7)° for II. The methoxy-bound phenyl rings (C16–C21) in I and II are inclined to the indole frameworks, subtending dihedral angles of 66.31 (15) and 77.70 (9)°, respectively. In I, the planes of these outer phenyl rings (C9–C14 and C16–C21) subtend an angle of 59.8 (2)°, while in II they are nearly orthogonal [86.9 (9)°]. In the latter case, the dihedral angle between two sulfonyl-bound phenyl rings (C9–C14 and C24–C29) is 54.4 (2)°. The torsion angles O2—S1—N1—C1 and O1—S1—N1—C8 [177.3 (3) and −159.7 (3)° for I and −160.5 (5) and 164.0 (5)° for II, respectively] indicate the anti-periplanar conformation of the sulfonyl moiety. The geometric parameters of compounds I and II agree well with those reported for related structures [Madhan et al., 2022 , 2023a ,b , 2024 ]. In both compounds, the tetrahedral configuration around atom S1 is slightly distorted. The increase in the O2—S1—O1 angle [119.83 (17)° in I and 120.1 (3)° in II], with a simultaneous decrease in the N1—S1—C9 angle [104.54 (15)° in I and 105.9 (3)° in II] from the ideal tetrahedral value (109.5°) are attributed to the Thorpe–Ingold effect (Bassindale, 1984 ). The widening of the angles may be due to the repulsive interaction between the two short S=O bonds. In both compounds, as a result of the electron-withdrawing character of the phenylsulfonyl group, the N—Csp² bond lengths [N1—C1 = 1.420 (4) in I and 1.429 (8) Å in II and N1—C8 = 1.427 (4) in I and 1.421 (7) Å in II] are longer than the mean value of 1.355 (14) Å for this bond (Allen et al., 1987 ; Cambridge Structural Database (CSD), Version 5.37; Groom et al., 2016 ). In both compounds, the sum of the bond angles around N1 [352.2 (2)° in I and 355.8 (2)° in II] indicate the sp² hybridization (Beddoes et al., 1986 ). In both compounds, the expansion of the ipso angles at atoms C1, C3 and C4, and the contraction of the apical angles at atoms C2, C5 and C6 is caused by fusion of the smaller pyrrole ring with the six-membered benzene ring and the strain is taken up by angular distortion rather than by bond-length distortion (Allen, 1981 ).

Figure 1
The molecular structure of compound I, with atom labelling and displacement ellipsoids drawn at the 30% probability level. The dashed line indicates the intramolecular hydrogen bond.

Figure 2
The molecular structure of compound II, with atom labelling and displacement ellipsoids drawn at the 30% probability level. The dashed lines indicate the intramolecular hydrogen bonds.

The molecular conformation of compound I is stabilized by the weak intramolecular hydrogen bond C2—H2⋯O1 [C2⋯O1 = 2.993 (5) Å] formed by the sulfone O atom, which generates an S(6) (N1/S1/O1/C1/C2/H2) ring motif (Fig. 1). A similar interaction in compound II [C2⋯O1 = 2.886 (9) Å] is accompanied by two additional intramolecular bonds involving methylene donors and sulfone [C15⋯O2 = 2.948 (8) Å] and methoxyphenyl [C15⋯O4 = 2.862 (8) Å] O atoms, which in total generate three S(6) ring motifs (N1/S1/O1/C1/C2/H2, N1/S1/O2/C8/C15/H15B) and N2/C16/C21/O4/C15/H15A), respectively (Fig. 2).

3. Supramolecular features

With a lack of conventional hydrogen-bond donor functionality, the supramolecular structures of both compounds are dominated by C—H⋯O bonding (Tables 1 and 2), whereas π–π interactions are specific for I and weaker C—H⋯π bonds are relevant for II only. In the crystal of I, the shortest hydrogen-bond contacts are observed for acetyl O-atom acceptors [C17⋯O4ⁱⁱⁱ = 3.312 (4) Å, symmetry code: (iii) −x + 2, −y + 1, −z + 1]. Such bonds assemble pairs of the molecules into centrosymmetric dimers (Fig. 3) with a cyclic R₂²(12) (Bernstein et al., 1995 ) ring motif. The dimers are further interconnected into chains propagating along the a-direction through double π–π interactions of the indole ring systems (Fig. 3). The components of such stacks are related by inversion and therefore two indole systems are parallel, with interplanar separation of 3.517 (4) Å. However, the overlap is only partial, as it is indicated by relatively large intercentroid distances [Cg1⋯Cg2^iv = 3.801 (5) Å; Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively; symmetry code: (iv) −x + 1, −y + 1, −z + 1] and slippage angle of 22.3 (3)°. These parameters agree well with those for π–π interactions seen in the crystal structures of comparable 1-(phenylsulfonyl)-1H-indole derivatives (Madhan et al., 2024). Three C—H⋯O bonds with sulfone O-atom acceptors [C⋯O = 3.410 (5)–3.537 (4) Å; Table 1] are important for connection of the above chains into layers parallel to the ac plane (Fig. 4) and separated by 9.890 Å, which is half of the b-axis parameter of the unit cell. Only one C—H⋯O bond occurs between the layers, involving the sterically most accessible acetyl O-atom acceptor [C12⋯O4ⁱⁱ = 3.527 (6) Å; symmetry code: (ii) x, −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ]. No significant C—H⋯π interactions with C⋯centroid distances below 4 Å are observed in the structure.

Table 1
Hydrogen-bond geometry (Å, °) for I

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.41	2.993 (5)	120
C5—H5⋯O1ⁱ	0.93	2.75	3.530 (5)	143
C7—H7⋯O1ⁱ	0.93	2.81	3.537 (4)	135
C12—H12⋯O4ⁱⁱ	0.93	2.62	3.527 (6)	164
C13—H13⋯O3ⁱⁱⁱ	0.93	2.69	3.591 (7)	164
C17—H17⋯O4ⁱⁱⁱ	0.93	2.42	3.312 (4)	161
C24—H24B⋯O2ⁱ	0.96	2.49	3.410 (5)	160
Symmetry codes: (i) ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) .

Table 2
Hydrogen-bond geometry (Å, °) for II

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.30	2.886 (9)	121
C15—H15A⋯O4	0.97	2.23	2.862 (8)	122
C15—H15B⋯O2	0.97	2.34	2.948 (8)	120
C10—H10⋯O5ⁱ	0.93	2.93	3.719 (9)	144
C11—H11⋯O6ⁱ	0.93	2.85	3.723 (11)	156
C15—H15A⋯O1ⁱⁱ	0.97	2.68	3.333 (8)	125
C19—H19⋯O2ⁱⁱⁱ	0.93	2.96	3.647 (9)	132
C20—H20⋯O5ⁱⁱⁱ	0.93	2.88	3.788 (8)	165
C28—H28⋯O6ⁱⁱ	0.93	2.79	3.716 (9)	171
C23—H23C⋯Cg1ⁱⁱ	0.96	2.96	3.701 (3)	135
C25—H25⋯Cg2^iv	0.93	2.67	3.483 (5)	147
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 3
Fragment of non-covalent chain propagating along the a-axis direction in the structure of I, with the pairs of the inversion-related adjacent molecules linked by double C—H⋯O bonds (dotted blue lines) and double π–π interactions (solid blue lines). [Symmetry codes: (iii) −x + 2, −y + 1, −z + 1; (iv) x + 1, −y + 1, −z + 1.]

Figure 4
Projection of the structure of I on the ac plane, showing the layer assembled with C—H⋯O and π–π bonds. [Symmetry codes: (i) x, y, z − 1; (v) x, y, z + 1.]

Similar non-covalent layers parallel to the ac plane are also seen in compound II (Fig. 5). However, the bonding pattern differs as π–π interactions are replaced by C—H⋯π interactions (on both axial sides of the indole system) and more extensive C—H⋯O bonding (Table 2). This is in line with increased number of hydrogen-bond donors and acceptors due to the incorporation of the additional phenylsulfonyl groups. The layers are sustained by a number of C—H⋯O interactions, which are relatively weak and distal [C⋯O = 3.503 (9)–3.788 (8)Å]. Significantly shorter contacts adopted by methyl groups are also present: C23⋯O1^v = 3.199 (7) Å; symmetry code: (v) x, y, z + 1. As a result of inappropriate angles at the H atoms, these contacts are not regarded as hydrogen bonds, rather representing a kind of tetrel interaction CH₃⋯O. A salient feature of the layer concerns C—H⋯π interactions involving the C1–C6 rings, which are appreciably short and directional [C25⋯Cg2^iv = 3.483 (5) Å; C25—H25⋯Cg2^iv = 147°; Cg2 is the C1–C6 ring centroid; symmetry code: (iv) x − $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ]. The shortest interlayer interactions represent C—H⋯O bonds with the most polarized methylene donors [C15⋯O1ⁱⁱ = 3.333 (8) Å; symmetry code: (ii) x, −y + 2, z + $[{1\over 2}]$ ], which act in synergy with a set of longer C—H⋯O (phenyl) bonds and weak C—H⋯π bonds to the indole (N1/C1/C6–C8) acceptors (Fig. 6). In comparison with the structure of I, the much more extensive interactions in the present case result in a lower interlayer spacing of 8.596 Å, which is a half of the b- axis parameter of the unit cell. This contributes to a slightly higher packing index of 68.1% versus 66.9% for I. However, in both the cases, the packing indices approach the lower limit of the 65–75% range expected for organic solids (Dunitz, 1995 ), suggesting relatively loose packing of these sterically strained molecules.

Figure 5
The non-covalent layer in the structure of II, viewed in a projection on the ac plane. Dotted blue lines represent CH⋯O bonds and short tetrel bonds C23⋯O1^v, while blue areas indicate short C—H⋯π bonds with the sulfonyl-bound phenyl donors situated nearly orthogonal to the plane of the drawing. [Symmetry codes: (i) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z − $[{1\over 2}]$ ; (iii) x + $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ; (iv) x − $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ ; (v) x, y, z + 1.]

Figure 6
Set of interlayer bonds in the structure of II, with the C—H⋯O and C—H⋯π bonds marked with dashed blue and red lines, respectively. Blue strips indicate two successive layers, which are nearly orthogonal to the plane of the drawing. [Symmetry codes: (ii) x, −y + 2, z + $[{1\over 2}]$ ; (iv) x − $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ .]

4. Hirshfeld surface analysis

The Hirshfeld surface calculations and associated two-dimensional fingerprint plots for I and II were performed in accord with established procedures (Tan et al., 2019 ) using Crystal Explorer (Spackman et al., 2021 ) to determine the influence of weak intermolecular interactions upon the molecular packing in the absence of conventional hydrogen bonds. The Hirshfeld surfaces for two compounds mapped over d_norm using a fixed colour scale of −0.249 (red) to 1.450 a.u. (blue) for I and −0.096 (red) to 1.442 a.u. (blue) for II are shown in Fig. 7. One can note a relatively scarce landscape of short contacts that is particularly the case for II, which shows normal van der Waals separations only (denoted with several white regions on the surface). The few red spots present in the case I indicate intermolecular contacts involved in weak hydrogen bonding.

Figure 7
The Hirshfeld surfaces of compounds I and II mapped over d_norm.

The two-dimensional fingerprint plots (Parkin et al., 2007 ) detailing the various interactions for the molecules are shown in Fig. 8. For both compounds, the Hirshfeld surfaces suggest dominance of contacts with hydrogen atoms, accounting for over 85% of the contacts. Beyond the largest fractions of H⋯H contacts (48.8 and 44.6%), these short separations are overwhelmingly O⋯H/H⋯O and C⋯H/H⋯C, which contribute 22.4 and 21.7%, respectively, to the Hirshfeld surface in I and 25.8 and 26.8%, respectively, in II, respectively. The plots also illustrate the finding discussed above that the structure of II exhibits a larger number, but essentially weaker C—H⋯O bonds. Thus, for I the O⋯H/H⋯O plot represents pair of broad spikes pointing to the lower left, with the shortest contact being 2.35 Å, whereas in the case of II the diffuse and faintly discernible spikes are much shorter (O⋯H = 2.70 Å). The larger contribution of C⋯H/H⋯C contacts for II (Fig. 8) reflects the increased significance of C—H⋯π interactions for the crystal packing, in line with increased number of aromatic groups. The small fraction of N⋯H/H⋯N contacts (1.3%) is also a consequence of C—H⋯π bonding, namely with the pyrrole ring acceptor. An overlap between the parallel indole ring systems in I, due to the slipped π–π interactions, is clearly indicated by the plots for C⋯C, N⋯C/C⋯N and O⋯C/C⋯O (total contribution is 7.1%), in the form of the blue areas centered at ca d_e = d_i = 1.90 Å and with shortest contacts of 3.50 Å (Fig. 8). This weak bonding complements the above interactions involving H atoms. For both compounds, the H⋯H intermolecular contacts predominate, followed by the C⋯H/H⋯C and O⋯H/H⋯O contacts. The Hirshfeld surface analysis confirms the importance of distal H-atom contacts (and contacts associated with the π–π interaction for I) in establishing the packing.

Figure 8
Two-dimensional fingerprint plots for I and II and those delineated into the principal contributions of H⋯H, C⋯H/H⋯C, O⋯H/H⋯O, N⋯H/H⋯N, C⋯C, O⋯C/C⋯O and N⋯C/C⋯N contacts. Other contributors account for less than 1.0% contacts to the surface areas.

5. Database survey

A search of the Cambridge Structural Database (Version 5.37; Groom et al., 2016) indicated 123 compounds incorporating the phenylsulfonyl-1H-indole moiety. Of these, the most closely related examples are provided by structures of bromo-substituted 3-methyl-1-(phenylsulfonyl)-1H-indole derivatives (JOMJII, JOMJAA and JOMJEE; Madhan et al., 2024), ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate (HUCQUS; Gunasekaran et al., 2009 ), 3-iodo-2-methyl-1-phenylsulfonyl-1H-indole (ULESEK; Ramathilagam et al., 2011 ) and 1-(2-bromomethyl-1-phenylsulfonyl-1H-indol-3-yl)propan-1-one (CIQFEP; Umadevi et al., 2013 ). In these structures, the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring systems [the corresponding dihedral angles are in the range 73.35 (7)–89.91 (11)°], being comparable with those in the present two compounds.

6. Synthesis and crystallization

Compound I: 3-methoxy-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}aniline (0.100 g, 0.255 mmol) was dissolved in 5 ml of acetic anhydride and the reaction mixture was stirred for 8 h at 343 K. After completion of the reaction (monitored by TLC, R_f = 0.30, hexane–ethyl acetate 80:20 v/v), the solution was poured into crushed ice (50 g), the solid formed was filtered, washed with 100 ml of water and dried over anhydrous CaCl₂. Recrystallization of the crude product from diethyl ether (10 mL) afforded N-(3-methoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}acetamide as a colourless solid (84 mg, 76%), m.p. = 413–415 K. ¹H NMR (300 MHz, CDCl₃), δ, p.p.m.: 8.06 (d, J = 7.8 Hz, 1H), 7.74 (d, J = 7.8 Hz, 2H), 7.50–7.34 (m, 4H), 7.29–7.16 (m, 3H), 6.87–6.79 (m, 3H), 6.61 (s, 1H), 5.35 (s, 2H), 3.76 (s, 3H), 2.04 (s, 3H). ¹³C{¹H} NMR (75 MHz, CDCl₃), δ, p.p.m.: 170.7, 160.4, 144.2, 138.3, 137.1, 137.0, 133.7, 130.3, 129.5, 129.2, 126.3, 124.4, 123.7, 120.6, 119.7, 114.5, 113.4, 113.3, 110.4, 55.4, 48.2, 22.6.

Compound II: To a solution of 2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole (0.710 g, 2.040 mmol) in CH₃CN (10 ml), K₂CO₃ (0.422 g, 3.060 mmol) and N-(2,5-dimethoxyphenyl)benzenesulfonamide (0.717 g, 2.448 mmol) were added and the mixture was stirred at room temperature for 12 h. After completion of the reaction (monitored by TLC, R_f = 0.60, hexane-ethyl acetate 80:20 v/v), the mixture was poured into crushed ice (50 g) containing 1 mL of concentrated HCl solution. The mixture was extracted with ethyl acetate (2 × 20 ml), the extracts were washed with water (2 × 20 ml) and dried over anhydrous Na₂SO₄. Removal of the solvent in vacuo followed by trituration of the crude product with 5 ml of methanol afforded N-(2,5-dimethoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide (0.802 g, 70%) as colourless solid, m.p. = 409–411 K. ¹H NMR (300 MHz, CDCl₃), δ, p.p.m.: 7.95 (d, J = 7.8 Hz, 1H), 7.66–7.57 (m, 4H), 7.53–7.46 (m, 1H), 7.43–7.35 (m, 4H), 7.32–7.24 (m, 2H), 7.21–7.08 (m, 2H), 7.00–6.90 (m, 2H), 6.73 (dd, J₁ = 9.0 Hz, J₂ = 2.7 Hz, 1H), 6.63–6.54 (m, 1H), 5.23 (s, 2H), 3.65 (s, 3H), 3.24 (s, 3H). ¹³C{¹H} NMR (75 MHz, CDCl₃), δ, p.p.m.: 153.1, 150.1, 139.6, 138.3, 138.1, 137.3, 133.7, 132.5, 129.7, 129.2, 128.5, 127.7, 127.2, 126.3, 124.4, 123.8, 120.9, 118.9, 114.9, 114.5, 112.1, 111.6, 55.8, 55.3, 49.1.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All C-bound H atoms were positioned geometrically and constrained to ride on their parent atoms: C—H = 0.93–0.97 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Table 3
Experimental details

	I	II
Crystal data
Chemical formula	C₂₄H₂₂N₂O₄S	C₂₉H₂₆N₂O₆S₂
M_r	434.49	562.64
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, Cc
Temperature (K)	305	293
a, b, c (Å)	13.6698 (17), 19.781 (2), 8.1056 (10)	13.463 (9), 17.193 (12), 11.532 (7)
β (°)	99.388 (8)	94.844 (19)
V (Å³)	2162.4 (5)	2660 (3)
Z	4	4
Radiation type	Cu Kα	Mo Kα
μ (mm⁻¹)	1.61	0.25
Crystal size (mm)	0.16 × 0.13 × 0.04	0.33 × 0.22 × 0.11

Data collection
Diffractometer	Bruker D8 Venture Diffractometer	Bruker D8 Venture Diffractometer
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )	Multi-scan (SADABS; Krause et al., 2015)
T_min, T_max	0.634, 0.753	0.504, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	47234, 3963, 2595	42032, 5193, 4533
R_int	0.087	0.086
(sin θ/λ)_max (Å⁻¹)	0.604	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.179, 1.07	0.057, 0.154, 1.12
No. of reflections	3963	5193
No. of parameters	283	354
No. of restraints	0	2
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.41	1.17, −0.26
Absolute structure	–	Flack x determined using 1861 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	–	0.16 (4)
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXS2018/3 (Sheldrick, 2008 ), SHELXL2018/3 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), pubCIF (Westrip, 2010 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC references: 2368308; 2368307

Crystal structure: contains datablocks global, I, II. DOI: https://doi.org/10.1107/S2056989024006649/nu2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024006649/nu2006Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989024006649/nu2006IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024006649/nu2006Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989024006649/nu2006IIsup5.cml

checkCIF report

Computing details top

N-(3-Methoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}acetamide (I) top

Crystal data top

C₂₄H₂₂N₂O₄S	F(000) = 912
M_r = 434.49	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 13.6698 (17) Å	Cell parameters from 47234 reflections
b = 19.781 (2) Å	θ = 1.4–25.0°
c = 8.1056 (10) Å	µ = 1.61 mm⁻¹
β = 99.388 (8)°	T = 305 K
V = 2162.4 (5) Å³	Prism, colorless
Z = 4	0.16 × 0.13 × 0.04 mm

Data collection top

Bruker D8 Venture Diffractometer	2595 reflections with I > 2σ(I)
Radiation source: micro focus sealed tube	R_int = 0.087
ω and φ scans	θ_max = 68.6°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −16→16
T_min = 0.634, T_max = 0.753	k = −23→23
47234 measured reflections	l = −9→9
3963 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.179	w = 1/[σ²(F_o²) + (0.0662P)² + 2.3955P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3963 reflections	Δρ_max = 0.27 e Å⁻³
283 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints	Extinction correction: SHELXL2018/3 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0036 (4)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5527 (2)	0.58150 (16)	0.5180 (4)	0.0494 (8)
C2	0.4749 (3)	0.61289 (19)	0.5779 (5)	0.0613 (9)
H2	0.471182	0.613774	0.691426	0.074*
C3	0.4031 (3)	0.6428 (2)	0.4613 (5)	0.0727 (11)
H3	0.350636	0.665179	0.497364	0.087*
C4	0.4072 (3)	0.6402 (2)	0.2915 (5)	0.0781 (12)
H4	0.357245	0.660465	0.216034	0.094*
C5	0.4840 (3)	0.6083 (2)	0.2333 (5)	0.0673 (10)
H5	0.485845	0.606208	0.119252	0.081*
C6	0.5586 (2)	0.57918 (17)	0.3473 (4)	0.0513 (8)
C7	0.6486 (3)	0.54485 (18)	0.3303 (4)	0.0555 (8)
H7	0.670758	0.536369	0.229756	0.067*
C8	0.6960 (2)	0.52676 (16)	0.4825 (4)	0.0502 (8)
C9	0.7198 (3)	0.64340 (19)	0.8178 (4)	0.0599 (9)
C10	0.6621 (4)	0.6939 (2)	0.8699 (6)	0.0867 (13)
H10	0.600910	0.683953	0.899914	0.104*
C11	0.6973 (5)	0.7597 (3)	0.8766 (8)	0.1113 (19)
H11	0.659700	0.794043	0.913607	0.134*
C12	0.7863 (5)	0.7751 (3)	0.8299 (7)	0.1083 (18)
H12	0.808546	0.819604	0.833023	0.130*
C13	0.8418 (4)	0.7248 (3)	0.7790 (7)	0.1038 (17)
H13	0.902906	0.735134	0.748880	0.125*
C14	0.8097 (3)	0.6589 (2)	0.7709 (6)	0.0824 (12)
H14	0.848301	0.625099	0.734269	0.099*
C15	0.7907 (3)	0.48792 (19)	0.5282 (4)	0.0591 (9)
H15A	0.837940	0.514936	0.602804	0.071*
H15B	0.777940	0.446945	0.586890	0.071*
C16	0.8217 (2)	0.40106 (16)	0.3218 (4)	0.0484 (8)
C17	0.8897 (2)	0.35387 (16)	0.3928 (4)	0.0525 (8)
H17	0.943506	0.367152	0.471601	0.063*
C18	0.8780 (3)	0.28657 (17)	0.3468 (4)	0.0544 (8)
C19	0.7983 (3)	0.26690 (19)	0.2299 (5)	0.0618 (9)
H19	0.789780	0.221723	0.199177	0.074*
C20	0.7312 (3)	0.3150 (2)	0.1590 (5)	0.0672 (10)
H20	0.677551	0.301742	0.079824	0.081*
C21	0.7419 (3)	0.38218 (19)	0.2031 (4)	0.0607 (9)
H21	0.696470	0.414191	0.153903	0.073*
C22	0.9413 (4)	0.1736 (2)	0.3867 (6)	0.0915 (14)
H22A	0.879674	0.156372	0.411348	0.137*
H22B	0.995389	0.149874	0.452372	0.137*
H22C	0.943939	0.167330	0.270103	0.137*
C23	0.8979 (3)	0.51411 (18)	0.3257 (5)	0.0578 (9)
C24	0.9462 (3)	0.4928 (2)	0.1812 (5)	0.0687 (10)
H24A	0.992634	0.526852	0.159832	0.103*
H24B	0.896515	0.487187	0.083803	0.103*
H24C	0.980398	0.450824	0.207134	0.103*
N1	0.63700 (19)	0.54697 (14)	0.6039 (3)	0.0495 (7)
N2	0.8335 (2)	0.47013 (13)	0.3784 (3)	0.0516 (7)
O1	0.5933 (2)	0.55538 (14)	0.8893 (3)	0.0732 (8)
O2	0.7592 (2)	0.51507 (13)	0.8517 (3)	0.0735 (8)
O3	0.9487 (2)	0.24362 (12)	0.4258 (4)	0.0755 (8)
O4	0.9139 (2)	0.56971 (13)	0.3939 (4)	0.0815 (9)
S1	0.67746 (7)	0.55995 (5)	0.80653 (10)	0.0577 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0507 (18)	0.0488 (18)	0.0484 (18)	0.0017 (14)	0.0070 (14)	0.0016 (14)
C2	0.061 (2)	0.071 (2)	0.055 (2)	0.0074 (19)	0.0169 (17)	0.0000 (17)
C3	0.062 (2)	0.088 (3)	0.070 (3)	0.019 (2)	0.0174 (19)	0.004 (2)
C4	0.069 (2)	0.096 (3)	0.069 (3)	0.024 (2)	0.012 (2)	0.016 (2)
C5	0.066 (2)	0.083 (3)	0.053 (2)	0.014 (2)	0.0087 (17)	0.0099 (19)
C6	0.0535 (18)	0.0532 (19)	0.0469 (18)	0.0029 (15)	0.0074 (14)	0.0035 (14)
C7	0.062 (2)	0.062 (2)	0.0441 (18)	0.0094 (17)	0.0107 (15)	0.0019 (15)
C8	0.0541 (18)	0.0479 (18)	0.0489 (18)	0.0059 (15)	0.0094 (14)	−0.0045 (14)
C9	0.069 (2)	0.062 (2)	0.0469 (19)	0.0051 (18)	0.0015 (16)	−0.0058 (16)
C10	0.091 (3)	0.072 (3)	0.097 (3)	0.007 (2)	0.014 (3)	−0.022 (2)
C11	0.141 (5)	0.063 (3)	0.125 (5)	0.005 (3)	0.007 (4)	−0.030 (3)
C12	0.147 (5)	0.070 (3)	0.100 (4)	−0.029 (4)	−0.003 (4)	−0.009 (3)
C13	0.105 (4)	0.089 (4)	0.117 (4)	−0.033 (3)	0.018 (3)	−0.013 (3)
C14	0.078 (3)	0.078 (3)	0.093 (3)	−0.009 (2)	0.018 (2)	−0.015 (2)
C15	0.062 (2)	0.063 (2)	0.0498 (19)	0.0096 (17)	0.0032 (16)	−0.0078 (16)
C16	0.0477 (17)	0.0484 (18)	0.0498 (18)	−0.0023 (14)	0.0101 (14)	−0.0055 (14)
C17	0.0519 (18)	0.0469 (19)	0.0570 (19)	−0.0013 (15)	0.0035 (15)	−0.0051 (15)
C18	0.057 (2)	0.0495 (19)	0.057 (2)	0.0028 (16)	0.0110 (16)	0.0052 (15)
C19	0.072 (2)	0.052 (2)	0.063 (2)	−0.0132 (18)	0.0132 (18)	−0.0067 (17)
C20	0.066 (2)	0.068 (2)	0.063 (2)	−0.010 (2)	−0.0016 (18)	−0.0101 (19)
C21	0.059 (2)	0.062 (2)	0.059 (2)	0.0033 (18)	0.0037 (16)	−0.0056 (17)
C22	0.119 (4)	0.047 (2)	0.107 (4)	0.013 (2)	0.014 (3)	−0.001 (2)
C23	0.0501 (19)	0.051 (2)	0.070 (2)	0.0038 (16)	0.0001 (16)	−0.0033 (17)
C24	0.064 (2)	0.067 (2)	0.078 (3)	−0.0058 (19)	0.0183 (19)	0.005 (2)
N1	0.0545 (16)	0.0554 (16)	0.0385 (14)	0.0040 (13)	0.0077 (11)	−0.0023 (11)
N2	0.0515 (15)	0.0473 (15)	0.0566 (16)	0.0022 (13)	0.0101 (12)	−0.0067 (12)
O1	0.0866 (19)	0.0873 (19)	0.0511 (14)	−0.0085 (15)	0.0270 (13)	0.0007 (13)
O2	0.0924 (19)	0.0701 (17)	0.0512 (14)	0.0249 (15)	−0.0085 (13)	0.0035 (12)
O3	0.0819 (18)	0.0497 (15)	0.091 (2)	0.0084 (13)	0.0019 (15)	0.0007 (13)
O4	0.0768 (18)	0.0556 (16)	0.108 (2)	−0.0049 (14)	0.0034 (16)	−0.0171 (15)
S1	0.0714 (6)	0.0588 (6)	0.0420 (5)	0.0043 (4)	0.0062 (4)	−0.0007 (4)

Geometric parameters (Å, º) top

C1—C2	1.386 (5)	C15—N2	1.473 (4)
C1—C6	1.400 (4)	C15—H15A	0.9700
C1—N1	1.420 (4)	C15—H15B	0.9700
C2—C3	1.379 (5)	C16—C17	1.375 (5)
C2—H2	0.9300	C16—C21	1.383 (5)
C3—C4	1.387 (6)	C16—N2	1.442 (4)
C3—H3	0.9300	C17—C18	1.385 (5)
C4—C5	1.373 (5)	C17—H17	0.9300
C4—H4	0.9300	C18—O3	1.366 (4)
C5—C6	1.385 (5)	C18—C19	1.378 (5)
C5—H5	0.9300	C19—C20	1.380 (5)
C6—C7	1.431 (5)	C19—H19	0.9300
C7—C8	1.345 (4)	C20—C21	1.378 (5)
C7—H7	0.9300	C20—H20	0.9300
C8—N1	1.427 (4)	C21—H21	0.9300
C8—C15	1.499 (5)	C22—O3	1.420 (5)
C9—C14	1.380 (6)	C22—H22A	0.9600
C9—C10	1.381 (5)	C22—H22B	0.9600
C9—S1	1.746 (4)	C22—H22C	0.9600
C10—C11	1.386 (7)	C23—O4	1.234 (4)
C10—H10	0.9300	C23—N2	1.356 (4)
C11—C12	1.365 (8)	C23—C24	1.496 (5)
C11—H11	0.9300	C24—H24A	0.9600
C12—C13	1.357 (8)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.373 (6)	N1—S1	1.665 (3)
C13—H13	0.9300	O1—S1	1.426 (3)
C14—H14	0.9300	O2—S1	1.427 (3)

C2—C1—C6	122.1 (3)	H15A—C15—H15B	108.0
C2—C1—N1	130.7 (3)	C17—C16—C21	120.7 (3)
C6—C1—N1	107.2 (3)	C17—C16—N2	118.5 (3)
C3—C2—C1	116.9 (3)	C21—C16—N2	120.8 (3)
C3—C2—H2	121.5	C16—C17—C18	120.0 (3)
C1—C2—H2	121.5	C16—C17—H17	120.0
C2—C3—C4	121.7 (4)	C18—C17—H17	120.0
C2—C3—H3	119.2	O3—C18—C19	124.5 (3)
C4—C3—H3	119.2	O3—C18—C17	115.5 (3)
C5—C4—C3	121.0 (4)	C19—C18—C17	120.0 (3)
C5—C4—H4	119.5	C18—C19—C20	119.3 (3)
C3—C4—H4	119.5	C18—C19—H19	120.4
C4—C5—C6	118.9 (4)	C20—C19—H19	120.4
C4—C5—H5	120.6	C21—C20—C19	121.4 (3)
C6—C5—H5	120.6	C21—C20—H20	119.3
C5—C6—C1	119.4 (3)	C19—C20—H20	119.3
C5—C6—C7	133.1 (3)	C20—C21—C16	118.6 (3)
C1—C6—C7	107.5 (3)	C20—C21—H21	120.7
C8—C7—C6	109.3 (3)	C16—C21—H21	120.7
C8—C7—H7	125.3	O3—C22—H22A	109.5
C6—C7—H7	125.3	O3—C22—H22B	109.5
C7—C8—N1	108.4 (3)	H22A—C22—H22B	109.5
C7—C8—C15	129.1 (3)	O3—C22—H22C	109.5
N1—C8—C15	122.4 (3)	H22A—C22—H22C	109.5
C14—C9—C10	120.1 (4)	H22B—C22—H22C	109.5
C14—C9—S1	119.9 (3)	O4—C23—N2	120.5 (4)
C10—C9—S1	119.9 (3)	O4—C23—C24	122.2 (4)
C9—C10—C11	118.7 (5)	N2—C23—C24	117.3 (3)
C9—C10—H10	120.7	C23—C24—H24A	109.5
C11—C10—H10	120.7	C23—C24—H24B	109.5
C12—C11—C10	121.1 (5)	H24A—C24—H24B	109.5
C12—C11—H11	119.4	C23—C24—H24C	109.5
C10—C11—H11	119.4	H24A—C24—H24C	109.5
C13—C12—C11	119.3 (5)	H24B—C24—H24C	109.5
C13—C12—H12	120.4	C1—N1—C8	107.5 (2)
C11—C12—H12	120.4	C1—N1—S1	121.4 (2)
C12—C13—C14	121.4 (5)	C8—N1—S1	126.1 (2)
C12—C13—H13	119.3	C23—N2—C16	123.5 (3)
C14—C13—H13	119.3	C23—N2—C15	118.2 (3)
C13—C14—C9	119.4 (5)	C16—N2—C15	116.7 (3)
C13—C14—H14	120.3	C18—O3—C22	118.9 (3)
C9—C14—H14	120.3	O1—S1—O2	119.83 (17)
N2—C15—C8	111.2 (3)	O1—S1—N1	106.91 (15)
N2—C15—H15A	109.4	O2—S1—N1	106.10 (14)
C8—C15—H15A	109.4	O1—S1—C9	108.73 (18)
N2—C15—H15B	109.4	O2—S1—C9	109.62 (18)
C8—C15—H15B	109.4	N1—S1—C9	104.54 (15)

C6—C1—C2—C3	−0.7 (6)	N2—C16—C21—C20	−176.8 (3)
N1—C1—C2—C3	179.7 (4)	C2—C1—N1—C8	−177.6 (4)
C1—C2—C3—C4	1.5 (6)	C6—C1—N1—C8	2.7 (4)
C2—C3—C4—C5	−0.7 (7)	C2—C1—N1—S1	−21.1 (5)
C3—C4—C5—C6	−0.9 (7)	C6—C1—N1—S1	159.3 (2)
C4—C5—C6—C1	1.7 (6)	C7—C8—N1—C1	−2.7 (4)
C4—C5—C6—C7	−177.7 (4)	C15—C8—N1—C1	−179.1 (3)
C2—C1—C6—C5	−0.9 (5)	C7—C8—N1—S1	−157.9 (3)
N1—C1—C6—C5	178.8 (3)	C15—C8—N1—S1	25.7 (5)
C2—C1—C6—C7	178.6 (3)	O4—C23—N2—C16	−170.7 (3)
N1—C1—C6—C7	−1.7 (4)	C24—C23—N2—C16	10.4 (5)
C5—C6—C7—C8	179.4 (4)	O4—C23—N2—C15	−5.6 (5)
C1—C6—C7—C8	0.0 (4)	C24—C23—N2—C15	175.6 (3)
C6—C7—C8—N1	1.7 (4)	C17—C16—N2—C23	80.1 (4)
C6—C7—C8—C15	177.7 (3)	C21—C16—N2—C23	−102.1 (4)
C14—C9—C10—C11	−1.1 (7)	C17—C16—N2—C15	−85.2 (4)
S1—C9—C10—C11	−179.6 (4)	C21—C16—N2—C15	92.5 (4)
C9—C10—C11—C12	1.2 (8)	C8—C15—N2—C23	90.1 (4)
C10—C11—C12—C13	−1.2 (9)	C8—C15—N2—C16	−103.7 (3)
C11—C12—C13—C14	1.0 (9)	C19—C18—O3—C22	0.1 (6)
C12—C13—C14—C9	−0.9 (8)	C17—C18—O3—C22	179.4 (4)
C10—C9—C14—C13	0.9 (7)	C1—N1—S1—O1	48.3 (3)
S1—C9—C14—C13	179.5 (4)	C8—N1—S1—O1	−159.7 (3)
C7—C8—C15—N2	1.1 (5)	C1—N1—S1—O2	177.3 (3)
N1—C8—C15—N2	176.6 (3)	C8—N1—S1—O2	−30.7 (3)
C21—C16—C17—C18	−0.7 (5)	C1—N1—S1—C9	−66.9 (3)
N2—C16—C17—C18	177.0 (3)	C8—N1—S1—C9	85.1 (3)
C16—C17—C18—O3	−179.3 (3)	C14—C9—S1—O1	169.5 (3)
C16—C17—C18—C19	0.1 (5)	C10—C9—S1—O1	−11.9 (4)
O3—C18—C19—C20	179.7 (3)	C14—C9—S1—O2	36.8 (4)
C17—C18—C19—C20	0.4 (5)	C10—C9—S1—O2	−144.7 (3)
C18—C19—C20—C21	−0.3 (6)	C14—C9—S1—N1	−76.6 (3)
C19—C20—C21—C16	−0.4 (6)	C10—C9—S1—N1	102.0 (3)
C17—C16—C21—C20	0.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.41	2.993 (5)	120
C5—H5···O1ⁱ	0.93	2.75	3.530 (5)	143
C7—H7···O1ⁱ	0.93	2.81	3.537 (4)	135
C12—H12···O4ⁱⁱ	0.93	2.62	3.527 (6)	164
C13—H13···O3ⁱⁱⁱ	0.93	2.69	3.591 (7)	164
C17—H17···O4ⁱⁱⁱ	0.93	2.42	3.312 (4)	161
C24—H24B···O2ⁱ	0.96	2.49	3.410 (5)	160

Symmetry codes: (i) x, y, z−1; (ii) x, −y+3/2, z+1/2; (iii) −x+2, −y+1, −z+1.

N-(2,5-Dimethoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide (II) top

Crystal data top

C₂₉H₂₆N₂O₆S₂	F(000) = 1176
M_r = 562.64	D_x = 1.405 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 13.463 (9) Å	Cell parameters from 42032 reflections
b = 17.193 (12) Å	θ = 1.4–25.0°
c = 11.532 (7) Å	µ = 0.25 mm⁻¹
β = 94.844 (19)°	T = 293 K
V = 2660 (3) Å³	Prism, colorless
Z = 4	0.33 × 0.22 × 0.11 mm

Data collection top

Bruker D8 Venture Diffractometer	4533 reflections with I > 2σ(I)
Radiation source: micro focus sealed tube	R_int = 0.086
ω and φ scans	θ_max = 26.5°, θ_min = 3.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −16→16
T_min = 0.504, T_max = 0.745	k = −21→21
42032 measured reflections	l = −14→14
5193 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0731P)² + 3.4858P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
5193 reflections	Δρ_max = 1.17 e Å⁻³
354 parameters	Δρ_min = −0.26 e Å⁻³
2 restraints	Absolute structure: Flack x determined using 1861 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.16 (4)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5561 (5)	0.9136 (3)	0.2353 (5)	0.0405 (13)
C2	0.5964 (6)	0.9217 (4)	0.1289 (6)	0.0540 (16)
H2	0.555973	0.922012	0.059422	0.065*
C3	0.6984 (6)	0.9292 (4)	0.1301 (7)	0.0629 (19)
H3	0.727709	0.933603	0.060166	0.076*
C4	0.7585 (6)	0.9304 (5)	0.2352 (8)	0.068 (2)
H4	0.827185	0.935784	0.234498	0.081*
C5	0.7173 (5)	0.9237 (5)	0.3382 (8)	0.0611 (18)
H5	0.758088	0.924447	0.407445	0.073*
C6	0.6143 (5)	0.9157 (3)	0.3416 (6)	0.0457 (14)
C7	0.5506 (5)	0.9086 (4)	0.4325 (6)	0.0474 (15)
H7	0.571262	0.908568	0.511531	0.057*
C8	0.4548 (4)	0.9019 (3)	0.3871 (5)	0.0368 (12)
C9	0.3602 (5)	0.7823 (3)	0.1536 (5)	0.0419 (13)
C10	0.4339 (5)	0.7464 (4)	0.0981 (7)	0.0556 (17)
H10	0.484497	0.775373	0.068826	0.067*
C11	0.4316 (6)	0.6650 (4)	0.0862 (9)	0.070 (2)
H11	0.481400	0.639367	0.050114	0.084*
C12	0.3561 (7)	0.6243 (5)	0.1277 (8)	0.071 (2)
H12	0.354691	0.570506	0.119685	0.085*
C13	0.2819 (7)	0.6605 (5)	0.1812 (8)	0.074 (2)
H13	0.230384	0.631258	0.207941	0.088*
C14	0.2831 (6)	0.7404 (5)	0.1957 (6)	0.0608 (19)
H14	0.233290	0.765304	0.232769	0.073*
C15	0.3647 (5)	0.9029 (3)	0.4548 (5)	0.0400 (12)
H15A	0.381098	0.928997	0.528504	0.048*
H15B	0.312174	0.932270	0.411961	0.048*
C16	0.3950 (4)	0.7701 (3)	0.5439 (5)	0.0371 (12)
C17	0.4070 (5)	0.6956 (4)	0.4999 (5)	0.0443 (13)
H17	0.375102	0.681947	0.428127	0.053*
C18	0.4660 (5)	0.6420 (4)	0.5620 (6)	0.0481 (15)
C19	0.5150 (5)	0.6612 (4)	0.6672 (6)	0.0552 (17)
H19	0.555292	0.624805	0.707987	0.066*
C20	0.5043 (5)	0.7351 (4)	0.7125 (6)	0.0531 (16)
H20	0.537510	0.748217	0.783811	0.064*
C21	0.4437 (4)	0.7899 (4)	0.6516 (5)	0.0422 (13)
C22	0.4410 (7)	0.5443 (5)	0.4146 (8)	0.074 (2)
H22A	0.461365	0.581454	0.359113	0.110*
H22B	0.369542	0.542977	0.411544	0.110*
H22C	0.465569	0.493729	0.396292	0.110*
C23	0.4596 (8)	0.8823 (5)	0.8082 (7)	0.077 (2)
H23A	0.531027	0.880524	0.820273	0.115*
H23B	0.431424	0.845285	0.858364	0.115*
H23C	0.436809	0.933578	0.825521	0.115*
C24	0.1965 (4)	0.8362 (4)	0.6486 (5)	0.0415 (13)
C25	0.1984 (5)	0.7775 (4)	0.7286 (6)	0.0531 (16)
H25	0.206152	0.726136	0.705626	0.064*
C26	0.1887 (6)	0.7953 (5)	0.8457 (7)	0.067 (2)
H26	0.189399	0.755573	0.900444	0.081*
C27	0.1782 (6)	0.8710 (5)	0.8800 (7)	0.065 (2)
H27	0.172197	0.882626	0.957870	0.078*
C28	0.1766 (6)	0.9298 (5)	0.7985 (7)	0.065 (2)
H28	0.170116	0.981104	0.822519	0.077*
C29	0.1843 (5)	0.9143 (4)	0.6818 (7)	0.0540 (16)
H29	0.181569	0.954118	0.627016	0.065*
N1	0.4553 (4)	0.9058 (3)	0.2641 (4)	0.0389 (10)
N2	0.3279 (4)	0.8234 (3)	0.4772 (4)	0.0363 (10)
O1	0.3855 (4)	0.9166 (3)	0.0595 (4)	0.0592 (12)
O2	0.2718 (4)	0.9068 (3)	0.2140 (4)	0.0608 (13)
O3	0.4797 (5)	0.5658 (3)	0.5265 (5)	0.0713 (15)
O4	0.4295 (4)	0.8639 (3)	0.6904 (4)	0.0544 (11)
O5	0.1821 (3)	0.7351 (3)	0.4813 (4)	0.0556 (12)
O6	0.1575 (3)	0.8740 (3)	0.4303 (5)	0.0573 (12)
S1	0.36074 (11)	0.88404 (9)	0.16552 (11)	0.0423 (4)
S2	0.20853 (11)	0.81497 (9)	0.50035 (12)	0.0414 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.050 (3)	0.031 (3)	0.041 (3)	−0.009 (2)	0.010 (3)	0.000 (2)
C2	0.062 (4)	0.051 (4)	0.050 (4)	−0.011 (3)	0.011 (3)	−0.004 (3)
C3	0.070 (5)	0.057 (4)	0.065 (5)	−0.014 (4)	0.030 (4)	0.002 (3)
C4	0.053 (4)	0.063 (5)	0.089 (6)	−0.016 (3)	0.017 (4)	−0.007 (4)
C5	0.044 (3)	0.068 (5)	0.072 (5)	−0.011 (3)	0.004 (3)	0.003 (4)
C6	0.051 (3)	0.035 (3)	0.050 (4)	−0.005 (3)	−0.003 (3)	0.000 (2)
C7	0.048 (3)	0.052 (4)	0.041 (3)	−0.010 (3)	−0.004 (3)	0.003 (3)
C8	0.047 (3)	0.032 (3)	0.031 (3)	−0.005 (2)	0.002 (2)	−0.001 (2)
C9	0.042 (3)	0.041 (3)	0.040 (3)	−0.001 (3)	−0.010 (2)	−0.002 (3)
C10	0.043 (3)	0.050 (4)	0.074 (5)	−0.003 (3)	0.002 (3)	−0.011 (3)
C11	0.053 (4)	0.051 (4)	0.104 (7)	0.003 (3)	−0.008 (4)	−0.019 (4)
C12	0.086 (6)	0.050 (4)	0.074 (5)	−0.012 (4)	−0.011 (5)	−0.003 (4)
C13	0.091 (6)	0.067 (5)	0.064 (5)	−0.036 (5)	0.011 (4)	−0.003 (4)
C14	0.056 (4)	0.074 (5)	0.052 (4)	−0.007 (4)	0.003 (3)	−0.015 (3)
C15	0.049 (3)	0.035 (3)	0.036 (3)	0.001 (2)	0.003 (2)	−0.003 (2)
C16	0.039 (3)	0.041 (3)	0.032 (3)	−0.001 (2)	0.003 (2)	−0.003 (2)
C17	0.044 (3)	0.047 (3)	0.040 (3)	−0.006 (3)	−0.004 (2)	−0.003 (2)
C18	0.043 (3)	0.038 (3)	0.062 (4)	−0.003 (3)	0.002 (3)	0.003 (3)
C19	0.046 (4)	0.063 (4)	0.055 (4)	0.006 (3)	−0.007 (3)	0.013 (3)
C20	0.044 (3)	0.066 (4)	0.047 (4)	−0.003 (3)	−0.011 (3)	−0.001 (3)
C21	0.038 (3)	0.050 (3)	0.037 (3)	−0.003 (3)	0.000 (2)	−0.005 (2)
C22	0.071 (5)	0.056 (5)	0.092 (6)	−0.006 (4)	−0.005 (4)	−0.023 (4)
C23	0.104 (7)	0.079 (6)	0.044 (4)	0.005 (5)	−0.013 (4)	−0.018 (4)
C24	0.035 (3)	0.049 (3)	0.041 (3)	−0.006 (2)	0.006 (2)	−0.007 (2)
C25	0.062 (4)	0.049 (4)	0.049 (4)	−0.002 (3)	0.006 (3)	0.002 (3)
C26	0.078 (5)	0.080 (5)	0.044 (4)	−0.006 (4)	0.007 (4)	−0.001 (4)
C27	0.059 (4)	0.089 (6)	0.049 (4)	−0.008 (4)	0.010 (3)	−0.020 (4)
C28	0.060 (4)	0.064 (5)	0.071 (5)	−0.015 (4)	0.017 (4)	−0.027 (4)
C29	0.057 (4)	0.047 (3)	0.059 (4)	−0.012 (3)	0.015 (3)	−0.008 (3)
N1	0.042 (3)	0.042 (3)	0.032 (2)	−0.004 (2)	0.0000 (19)	−0.0013 (19)
N2	0.037 (2)	0.039 (2)	0.033 (2)	−0.0031 (19)	0.0025 (19)	0.0005 (18)
O1	0.083 (3)	0.055 (3)	0.037 (2)	0.001 (2)	−0.008 (2)	−0.002 (2)
O2	0.052 (3)	0.073 (3)	0.055 (3)	0.014 (2)	−0.009 (2)	−0.014 (2)
O3	0.084 (4)	0.048 (3)	0.081 (4)	0.010 (3)	−0.005 (3)	−0.003 (3)
O4	0.067 (3)	0.056 (3)	0.038 (2)	−0.003 (2)	−0.007 (2)	−0.0134 (19)
O5	0.055 (3)	0.065 (3)	0.045 (3)	−0.018 (2)	−0.001 (2)	−0.011 (2)
O6	0.046 (2)	0.069 (3)	0.055 (3)	0.007 (2)	−0.005 (2)	0.010 (2)
S1	0.0484 (8)	0.0465 (7)	0.0305 (7)	0.0067 (7)	−0.0057 (6)	−0.0013 (6)
S2	0.0377 (7)	0.0507 (8)	0.0350 (7)	−0.0053 (6)	−0.0013 (5)	−0.0019 (6)

Geometric parameters (Å, º) top

C1—C2	1.390 (9)	C17—H17	0.9300
C1—C6	1.398 (9)	C18—C19	1.371 (10)
C1—N1	1.429 (8)	C18—O3	1.389 (8)
C2—C3	1.379 (11)	C19—C20	1.385 (10)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.399 (13)	C20—C21	1.396 (9)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.358 (12)	C21—O4	1.368 (8)
C4—H4	0.9300	C22—O3	1.400 (10)
C5—C6	1.397 (10)	C22—H22A	0.9600
C5—H5	0.9300	C22—H22B	0.9600
C6—C7	1.416 (10)	C22—H22C	0.9600
C7—C8	1.355 (9)	C23—O4	1.420 (8)
C7—H7	0.9300	C23—H23A	0.9600
C8—N1	1.421 (7)	C23—H23B	0.9600
C8—C15	1.497 (8)	C23—H23C	0.9600
C9—C10	1.372 (10)	C24—C25	1.367 (9)
C9—C14	1.385 (10)	C24—C29	1.410 (9)
C9—S1	1.755 (6)	C24—S2	1.768 (6)
C10—C11	1.406 (10)	C25—C26	1.401 (10)
C10—H10	0.9300	C25—H25	0.9300
C11—C12	1.354 (13)	C26—C27	1.371 (12)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.367 (13)	C27—C28	1.380 (13)
C12—H12	0.9300	C27—H27	0.9300
C13—C14	1.383 (12)	C28—C29	1.385 (11)
C13—H13	0.9300	C28—H28	0.9300
C14—H14	0.9300	C29—H29	0.9300
C15—N2	1.484 (7)	N1—S1	1.676 (5)
C15—H15A	0.9700	N2—S2	1.658 (5)
C15—H15B	0.9700	O1—S1	1.410 (5)
C16—C17	1.392 (8)	O2—S1	1.419 (5)
C16—C21	1.397 (8)	O5—S2	1.431 (5)
C16—N2	1.459 (7)	O6—S2	1.436 (5)
C17—C18	1.377 (9)

C2—C1—C6	122.6 (6)	C18—C19—H19	120.1
C2—C1—N1	131.5 (6)	C20—C19—H19	120.1
C6—C1—N1	105.8 (5)	C19—C20—C21	120.2 (6)
C3—C2—C1	117.6 (7)	C19—C20—H20	119.9
C3—C2—H2	121.2	C21—C20—H20	119.9
C1—C2—H2	121.2	O4—C21—C20	123.7 (5)
C2—C3—C4	120.8 (7)	O4—C21—C16	116.7 (5)
C2—C3—H3	119.6	C20—C21—C16	119.6 (6)
C4—C3—H3	119.6	O3—C22—H22A	109.5
C5—C4—C3	120.5 (7)	O3—C22—H22B	109.5
C5—C4—H4	119.7	H22A—C22—H22B	109.5
C3—C4—H4	119.7	O3—C22—H22C	109.5
C4—C5—C6	120.8 (8)	H22A—C22—H22C	109.5
C4—C5—H5	119.6	H22B—C22—H22C	109.5
C6—C5—H5	119.6	O4—C23—H23A	109.5
C5—C6—C1	117.6 (7)	O4—C23—H23B	109.5
C5—C6—C7	134.0 (7)	H23A—C23—H23B	109.5
C1—C6—C7	108.5 (6)	O4—C23—H23C	109.5
C8—C7—C6	109.7 (6)	H23A—C23—H23C	109.5
C8—C7—H7	125.1	H23B—C23—H23C	109.5
C6—C7—H7	125.1	C25—C24—C29	121.1 (6)
C7—C8—N1	107.3 (5)	C25—C24—S2	120.2 (5)
C7—C8—C15	125.7 (5)	C29—C24—S2	118.8 (5)
N1—C8—C15	126.4 (5)	C24—C25—C26	119.4 (7)
C10—C9—C14	121.5 (6)	C24—C25—H25	120.3
C10—C9—S1	119.1 (5)	C26—C25—H25	120.3
C14—C9—S1	119.3 (6)	C27—C26—C25	120.4 (8)
C9—C10—C11	118.8 (7)	C27—C26—H26	119.8
C9—C10—H10	120.6	C25—C26—H26	119.8
C11—C10—H10	120.6	C26—C27—C28	119.7 (7)
C12—C11—C10	119.4 (8)	C26—C27—H27	120.2
C12—C11—H11	120.3	C28—C27—H27	120.2
C10—C11—H11	120.3	C27—C28—C29	121.5 (7)
C11—C12—C13	121.6 (7)	C27—C28—H28	119.3
C11—C12—H12	119.2	C29—C28—H28	119.3
C13—C12—H12	119.2	C28—C29—C24	117.9 (7)
C12—C13—C14	120.3 (8)	C28—C29—H29	121.1
C12—C13—H13	119.8	C24—C29—H29	121.1
C14—C13—H13	119.8	C8—N1—C1	108.7 (5)
C13—C14—C9	118.4 (7)	C8—N1—S1	126.8 (4)
C13—C14—H14	120.8	C1—N1—S1	123.0 (4)
C9—C14—H14	120.8	C16—N2—C15	118.0 (5)
N2—C15—C8	112.2 (5)	C16—N2—S2	115.2 (4)
N2—C15—H15A	109.2	C15—N2—S2	116.8 (4)
C8—C15—H15A	109.2	C18—O3—C22	118.2 (6)
N2—C15—H15B	109.2	C21—O4—C23	119.0 (6)
C8—C15—H15B	109.2	O1—S1—O2	120.1 (3)
H15A—C15—H15B	107.9	O1—S1—N1	106.1 (3)
C17—C16—C21	119.2 (5)	O2—S1—N1	106.8 (3)
C17—C16—N2	118.1 (5)	O1—S1—C9	109.1 (3)
C21—C16—N2	122.6 (5)	O2—S1—C9	107.9 (3)
C18—C17—C16	120.4 (6)	N1—S1—C9	105.9 (3)
C18—C17—H17	119.8	O5—S2—O6	119.4 (3)
C16—C17—H17	119.8	O5—S2—N2	106.9 (3)
C19—C18—C17	120.8 (6)	O6—S2—N2	105.8 (3)
C19—C18—O3	115.0 (6)	O5—S2—C24	107.7 (3)
C17—C18—O3	124.2 (6)	O6—S2—C24	108.6 (3)
C18—C19—C20	119.8 (6)	N2—S2—C24	107.9 (3)

C6—C1—C2—C3	2.4 (10)	C25—C24—C29—C28	1.4 (10)
N1—C1—C2—C3	179.0 (6)	S2—C24—C29—C28	−179.0 (6)
C1—C2—C3—C4	−1.4 (11)	C7—C8—N1—C1	1.2 (6)
C2—C3—C4—C5	0.3 (12)	C15—C8—N1—C1	172.4 (5)
C3—C4—C5—C6	−0.1 (12)	C7—C8—N1—S1	167.7 (4)
C4—C5—C6—C1	1.0 (10)	C15—C8—N1—S1	−21.2 (8)
C4—C5—C6—C7	−179.1 (8)	C2—C1—N1—C8	−178.1 (6)
C2—C1—C6—C5	−2.2 (9)	C6—C1—N1—C8	−1.1 (6)
N1—C1—C6—C5	−179.6 (6)	C2—C1—N1—S1	14.8 (9)
C2—C1—C6—C7	177.9 (6)	C6—C1—N1—S1	−168.1 (4)
N1—C1—C6—C7	0.5 (6)	C17—C16—N2—C15	−131.1 (6)
C5—C6—C7—C8	−179.7 (7)	C21—C16—N2—C15	51.7 (7)
C1—C6—C7—C8	0.2 (7)	C17—C16—N2—S2	84.4 (6)
C6—C7—C8—N1	−0.9 (7)	C21—C16—N2—S2	−92.8 (6)
C6—C7—C8—C15	−172.1 (5)	C8—C15—N2—C16	60.6 (6)
C14—C9—C10—C11	−1.3 (11)	C8—C15—N2—S2	−155.5 (4)
S1—C9—C10—C11	−178.4 (6)	C19—C18—O3—C22	−173.2 (7)
C9—C10—C11—C12	1.2 (12)	C17—C18—O3—C22	7.9 (10)
C10—C11—C12—C13	0.0 (13)	C20—C21—O4—C23	−13.8 (10)
C11—C12—C13—C14	−0.9 (13)	C16—C21—O4—C23	167.1 (7)
C12—C13—C14—C9	0.8 (12)	C8—N1—S1—O1	164.0 (5)
C10—C9—C14—C13	0.4 (11)	C1—N1—S1—O1	−31.3 (5)
S1—C9—C14—C13	177.4 (6)	C8—N1—S1—O2	34.8 (5)
C7—C8—C15—N2	−98.6 (7)	C1—N1—S1—O2	−160.5 (5)
N1—C8—C15—N2	91.8 (6)	C8—N1—S1—C9	−80.1 (5)
C21—C16—C17—C18	0.2 (9)	C1—N1—S1—C9	84.6 (5)
N2—C16—C17—C18	−177.1 (5)	C10—C9—S1—O1	41.5 (6)
C16—C17—C18—C19	−1.0 (10)	C14—C9—S1—O1	−135.6 (5)
C16—C17—C18—O3	177.9 (6)	C10—C9—S1—O2	173.5 (5)
C17—C18—C19—C20	0.8 (10)	C14—C9—S1—O2	−3.6 (6)
O3—C18—C19—C20	−178.2 (7)	C10—C9—S1—N1	−72.4 (6)
C18—C19—C20—C21	0.1 (11)	C14—C9—S1—N1	110.5 (5)
C19—C20—C21—O4	−179.9 (6)	C16—N2—S2—O5	−53.8 (4)
C19—C20—C21—C16	−0.8 (10)	C15—N2—S2—O5	161.2 (4)
C17—C16—C21—O4	179.8 (5)	C16—N2—S2—O6	177.9 (4)
N2—C16—C21—O4	−3.0 (8)	C15—N2—S2—O6	32.9 (5)
C17—C16—C21—C20	0.6 (9)	C16—N2—S2—C24	61.8 (5)
N2—C16—C21—C20	177.8 (5)	C15—N2—S2—C24	−83.2 (5)
C29—C24—C25—C26	−0.3 (10)	C25—C24—S2—O5	21.3 (6)
S2—C24—C25—C26	−180.0 (6)	C29—C24—S2—O5	−158.4 (5)
C24—C25—C26—C27	−0.6 (12)	C25—C24—S2—O6	151.9 (5)
C25—C26—C27—C28	0.4 (12)	C29—C24—S2—O6	−27.7 (6)
C26—C27—C28—C29	0.7 (12)	C25—C24—S2—N2	−93.8 (5)
C27—C28—C29—C24	−1.5 (11)	C29—C24—S2—N2	86.5 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/C1/C6–C8 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.30	2.886 (9)	121
C15—H15A···O4	0.97	2.23	2.862 (8)	122
C15—H15B···O2	0.97	2.34	2.948 (8)	120
C10—H10···O5ⁱ	0.93	2.93	3.719 (9)	144
C11—H11···O6ⁱ	0.93	2.85	3.723 (11)	156
C15—H15A···O1ⁱⁱ	0.97	2.68	3.333 (8)	125
C19—H19···O2ⁱⁱⁱ	0.93	2.96	3.647 (9)	132
C20—H20···O5ⁱⁱⁱ	0.93	2.88	3.788 (8)	165
C28—H28···O6ⁱⁱ	0.93	2.79	3.716 (9)	171
C23—H23C···Cg1ⁱⁱ	0.96	2.96	3.701 (3)	135
C25—H25···Cg2^iv	0.93	2.67	3.483 (5)	147

Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x, −y+2, z+1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) x−1/2, −y+3/2, z+1/2.

Acknowledgements

The authors thank the SAIF, IIT, Madras, India, for the data collection.

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure determination and Hirshfeld surface analysis of N-acetyl-N-3-meth­­oxy­phenyl and N-(2,5-di­meth­­oxy­phen­yl)-N-phenyl­sulfonyl derivatives of N-[1-(phenyl­sulfon­yl)-1H-indol-2-yl]methanamine

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Hirshfeld surface analysis

5. Database survey

6. Synthesis and crystallization

7. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure determination and Hirshfeld surface analysis of N-acetyl-N-3-methoxyphenyl and N-(2,5-dimethoxyphenyl)-N-phenylsulfonyl derivatives of N-[1-(phenylsulfonyl)-1H-indol-2-yl]methanamine

3. Supramolecular features